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Squaric acid

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Identification
Molecular formula
C4H2O4
CAS number
2892-51-5
IUPAC name
3,4-dihydroxycyclobut-3-ene-1,2-dione
State
State
Squaric acid is typically observed as a solid at room temperature, existing as white crystalline powder.
Melting point (Celsius)
186.00
Melting point (Kelvin)
459.15
Boiling point (Celsius)
230.00
Boiling point (Kelvin)
503.15
General information
Molecular weight
114.05g/mol
Molar mass
114.0480g/mol
Density
1.6540g/cm3
Appearence

Squaric acid is a white crystalline solid. It typically presents as a fine powder and is notable for its highly symmetrical structure and potential for hydrogen bonding.

Comment on solubility

Solubility of 3,4-dihydroxycyclobut-3-ene-1,2-dione

The solubility of 3,4-dihydroxycyclobut-3-ene-1,2-dione in various solvents presents interesting characteristics due to its unique molecular structure. Here are some key points regarding its solubility:

  • Water Solubility: This compound exhibits moderate solubility in water, primarily due to the presence of hydroxyl (-OH) groups which can form hydrogen bonds with water molecules.
  • Organic Solvents: It commonly shows enhanced solubility in polar organic solvents such as methanol and ethanol, again attributable to hydrogen bonding capabilities.
  • Temperature Dependence: The solubility may increase with temperature, making it important to consider conditions when working with the compound.
  • pH Influence: Variations in pH can impact its solubility; the presence of acidic or basic conditions may alter the ionization of hydroxyl groups, potentially affecting overall solubility.

In summary, the solubility of 3,4-dihydroxycyclobut-3-ene-1,2-dione can be significantly influenced by the choice of solvent, temperature, and pH. Understanding these factors is crucial for practical applications in synthesis and extraction processes.

Interesting facts

Interesting Facts about 3,4-Dihydroxycyclobut-3-ene-1,2-dione

The compound 3,4-dihydroxycyclobut-3-ene-1,2-dione is a fascinating example of a small cyclic diones, showcasing unique structural and reactivity characteristics that intrigue chemists. Here are some interesting aspects to consider:

  • Cyclic Structure: The cyclic nature of this compound allows it to participate in various chemical reactions, often leading to valuable transformations. Its ring strain can result in unexpected reactivity.
  • Functional Groups: With two hydroxyl groups and a dione in its structure, it is a prime candidate for exploring hydrogen bonding and is involved in many organic synthesis reactions.
  • Potential Applications: Due to its unique structural features, this compound could play a significant role in organic photochemistry. It serves as an important model for understanding interactions in more complex biological systems.
  • Research Interest: Scientists have shown increasing interest in compounds like this for their properties in drug development and materials science, as they can lead to the discovery of novel pharmaceuticals and materials.
  • Isomerization: The compound is thought to undergo various types of isomerization, which can have significant implications when considering its behavior in chemical reactions.

As you dive deeper into the study of 3,4-dihydroxycyclobut-3-ene-1,2-dione, one cannot overlook the profound implications such compounds have on our understanding of synthetic organic chemistry. Its fascinating structure serves as a reminder of the intricate designs nature has to offer through chemistry.

Synonyms
Squaric acid
3,4-Dihydroxy-3-cyclobutene-1,2-dione
2892-51-5
Quadratic acid
3,4-dihydroxycyclobut-3-ene-1,2-dione
3-Cyclobutene-1,2-dione, 3,4-dihydroxy-
Quadratsaeure
Cyclobutenedione, dihydroxy-
1,2-Diketo-3,4-dihydroxycyclobutene
Dihydroxycyclobutenedione
1,2-Dihydroxycyclobutene-3,4-dione
3,4-Dihydroxy-cyclobutene-1,2-dione
CCRIS 6793
NSC 125692
SVR9D0VODW
UNII-SVR9D0VODW
EINECS 220-761-4
CYCLOBUTENE-1,2-DIONE, 3,4-DIHYDROXY-
BRN 0774275
DTXSID9049409
AI3-61444
1,2-dioxo-3,4-dihydroxycyclobutene
SQUARIC ACID [MI]
1,2-DIHYDROXY CYCLOBUTENEDIONE
NSC-125692
3,4-Dihydroxy-3-cyclobuten-1,2-dion
1,2-dioxo-3,4-dihydroxycyclobut-3-ene
SQUARIC ACID [WHO-DD]
DTXCID8029369
CHEBI:52141
3,4-Dihydroxy-3-cyclobuten-1,2-dion [IUPAC]
4-08-00-02701 (Beilstein Handbook Reference)
3-Cyclobutene-1,2-dione,3,4-dihydroxy-
Diketocyclobutenediol
3,4-Dihydroxy-3-cyclobuten-1,2-dion (IUPAC)
Cyclobutenedione, dihydroxy
1,2Dihydroxycyclobutenedione
3,4Dihydroxy3cyclobuten1,2dion
1,2Dihydroxycyclobutene3,4dione
3,4Dihydroxycyclobutene1,2dione
1,2Diketo3,4dihydroxycyclobutene
3,4Dihydroxy3cyclobutene1,2dione
Cyclobutenedione, dihydroxy (8CI)
Cyclobutenedione, dihydroxy-(8CI)
Cyclobutene1,2dione, 3,4dihydroxy
3Cyclobutene1,2dione, 3,4dihydroxy
inchi=1/c4h2o4/c5-1-2(6)4(8)3(1)7/h5-6
pwebuxctkowpcw-uhfffaoysa-n
dihydroxycyclobut-3-ene-1,2-dione
Cyclobutanetetrone
MFCD00001334
1,2-Dihydroxycyclobutenedione
NSC624671
3,4-dihydroxy-3-cyclobutene-2-dione;QUADRATIC ACID
31150-56-8
1,2-DIHYDROXY-1-CYCLOBUTEN-3,4-DIONE
3,2-dione
1,4-dihydroxycyclobutene
WLN: L4VVTJ CQ DQ
SCHEMBL56172
76719-54-5
Cyclobutene-1, 3,4-dihydroxy-
DTXSID10420518
cyclobutenedione, 3,4-dihydroxy-
3-Cyclobutene-1, 3,4-dihydroxy-
STR05257
Tox21_202819
1,2-Dihydroxy-3,4-cyclobutenedione
BBL011240
NSC125692
STK936793
1-Cyclobutene-3,4-dione-1,2-diol
AKOS000121580
CS-W019969
FD13829
NSC 624671
NSC-624671
SB11012
1,2-dihydroxy-l-cyclobutene-3,4-dione
3,4-dihydroxy-3-cyclobuten-1,2-dione
1,2-dihydroxy-1-cyclobutene-3,4-dione
NCGC00260365-01
AC-22924
BP-10690
SY002206
3,4-dihydroxy-cyclobut-3-ene-1,2-dione
CAS-2892-51-5
DB-028257
D1399
NS00028581
EN300-16613
3,4-Dihydroxy-3-cyclobutene-1,2-dione, 99%
Q903298
Q3008466
Z56347217
F0001-0904
3,4-Dihydroxy-3-cyclobutene-1,2-dione, Lonza quality, 98.50-101.00% (w/w) (HPLC)